


A Night We’ll Never Forget

by Winchesterlovr0508



Category: Supernatural
Genre: Dean Winchester needs to use his words, Dean Winchester/Castiel First kiss, Friends to Lovers, Frottage, Gay Sex, M/M, Openly Bisexual Dean, Openly Gay Castiel, Smut, Top!Castiel, bottom! dean, porn with a plot
Language: English
Status: Completed
Published: 2019-12-21
Updated: 2019-12-21
Packaged: 2021-02-26 03:40:36
Rating: Not Rated
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,375
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21886816
Author URL: https://archiveofourown.org/users/Winchesterlovr0508/pseuds/Winchesterlovr0508
Summary: Dean Winchester realizes one day that he’s in love with his best friend and roommate Cas Novak.
Relationships: Destiel
Comments: 2
Kudos: 95
Collections: Destiel Smash Fest





	A Night We’ll Never Forget

**Author's Note:**

  * For [CeliPuff](https://archiveofourown.org/users/CeliPuff/gifts).



Let me tell about the cluster fuck that is my love life. Hey, name’s Dean. I’m just your regular down to earth guy who likes classic rock, muscle cars and I happen to be in love with my best friend. Not that _he’d_ notice. Anyways, a little backstory. 

Cas and I have been _besties_ since high school. We were there for each other through it all. When my parents died, when his dad turned out to be a grade A douchebag, we were there to soften the blow. Then college happened, we were roomies but I was kind of a dick back then. _Ok!_ I was a _huge_ dick back then! No need to rub it in, I’ve learned my lesson. _Moving on!_ Well, I didn’t treat Cas very well and we fell out for a little bit until I pried my head from my ass and apologized. He forgave me… _eventually,_ and we’ve been inseparable ever since.

I don’t know how or why it happened but I remember when. We were watching our favorite show, _Dr Sexy M.D_ and Cas was leaning back on his side of the couch. His jet black hair falling in his face and the five o’clock shadow making his electric blue eyes burn through my soul. “I just don’t know if they work together Dean.” 

The way he said my name sent a chill up my spine and woke up my dormant cock but I managed to play it cool. “What the hell are you talking about!? Celessica is made to last! It’s the best ship on the damn show Cas! You blind?”

Cas rolled his eyes and leaned toward me. I bit my lip when his vanilla scent invaded my senses. _Ok, so this is not a drill. I really wanna fuck Cas right now. So… that’s a thing._ I barely heard his words as he said them because I was too just looking at his lips and imagining them _everywhere._ “Celia is laid back and easy going and Jessica is like the exact opposite.” 

Now at this point I should mention that Cas was gay and he _loved_ flirting. Me? I swing both ways but I’m _always_ on top. And I know for a fact, Cas is a top too. So how would that work you ask? I have absolutely no fucking clue. Now back to your regularly scheduled panic attack. 

I have no clue _how_ my brain managed to keep up with the conversation while caveman me was imagining Cas bent over six ways to Sunday but I guess I’m just awesome like that. “That’s exactly why they work! They balance each other out. I mean look at us Cas.” _Oh fuck! Abort Winchester! Abort!_

Cas smiled cooly and bore those shocking blue eyes into me. “Yeah, just look at us. An angel and an Assbutt. And yet, we work don’t we Dean?”

He was making fun of me but my dick didn’t get the memo. It was maintaining a full salute at this point and I _had_ to get out of there. Fast. Saved by the end credits! Yes!

“Suck my dick Cas.” I got up from the couch uhh, we’ll say _gracefully._ Yeah. Shut up. I’m telling the story here. I walked down the hallway and headed towards my room. 

Cas called out, “Is that an invitation?”

I shut my door and stared at the pitch black ceiling. Definitely not thinking about Cas’ lips and definitely _not_ stroking my cock while imagining him sucking me off. Eventually I fell asleep and the next morning things were more or less the same. Only difference was I still wanted my best friend in a very biblical way. 

That weekend we headed to the local watering hole Roadhouse to meet our friends. Benny, Charlie and Balt, or as we called him _The Gay Disaster_ because of all the horrible situations his dick got him into, we’re waiting for us at our usual table. It was a great time. We drank, we played pool, we danced, did I mention we drank? Like… a lot. 

Cas and I crawled in an Uber and headed home. Once we got there we both immediately went to our rooms and went to bed. Around 4 in the morning I woke up, still drunk and feeling brave. _Too brave_. I went into Cas’ room and heard him snoring softly. I stumbled to his bed and like the genius I am whispered, “Cas? You awake?” 

Cas grumbled softly but didn’t respond otherwise, so I tried again. This time I succeeded at my smooth attempt to wake him up. “No Dean, I’m not awake. I’m actually training to die.” Even coming out of a dead sleep he was a smart ass. I opted not to say anything but crawled under the covers next to him. Our eyes had adjusted to the dark so when he turned on his side to look at me, I could just make out his curious silhouette looking at me. Of course, now was the moment I decided to keep my mouth shut. 

Cas didn’t say anything either, I guess neither of us trusted ourselves to speak, but he slowly raised his hand and glided it up my arm giving me goosebumps and waking up every nerve in my body. I inched awkwardly closer to him and soon our lips were just out of reach of each other. He must’ve been just as nervous because his breathing was ragged like he had just got done with another one of his runs. 

My heart pounded in my chest, I mean, was this _really_ happening? Had Cas always wanted this too? Or did he just get smacked in the face with feels one day like I did? Whatever it was, I didn’t see any doubt in his eyes. I took a gulp and steeled my nerves. _Now or never… right?_

I’ll spare you the saucy details but I’ll just say… our dicks touched. A lot. That sounds really weird out of context. Ok, I guess I _will_ give you the saucy details. 

The Great Sword Fight of 2019 began when Cas was on top of me, grinding his crotch against mine with our tongues dancing to the death. Trust me folks, when I say it was _hot,_ I mean it was H-O-T hot. I was ready to blow before my pants even came off. Well, before I knew it, those were off. Actually, all my clothes were off and I don’t exactly remember how that happened. What I _do_ remember is Cas gripping my cock in his massive hand and breathing lustfully in my ear, “What do you want Dean?”

I muttered something that was supposed to sound like “You” before I clenched his obsidian hair in one hand and his ass in the other. Looking back on it, I was totally Cas’ bitch that night but I didn’t care, I just wanted _him._ Top or bottom didn’t matter to me. Every nerve in my body craved Cas and _wow,_ did he oblige. 

Without another word, he gripped both our cocks and began expertly grinding against me while stroking up and down, making it impossible for me to see clearly. You know beer goggles? Yeah… try wearing fuck goggles. It was amazing. Before I knew it, I felt the familiar tug in my gut as I was about to come. Cas must’ve been close too because he began moving and stroking faster, his head fell back as he moaned my name. When that sound hit my ears it was all over for us both. I barely gasped out, “Cas!” before he was working through both of our orgasms. I painted his hand and my chest with milky white fluid and started seeing spots. Cas licked a drop of come off his hand and leaned down to kiss me, tasting mine and his come on his lips sent a shock through my body. 

I stayed laying on my back as he cleaned us off with a t shirt (which of course ended up being mine) and he nestled his head into my chest and quickly began softly snoring in my arms. Now between you and me, I could’ve stayed like that forever, but morning came and ruined everything. 

I woke up in Cas’ bed alone and quickly found out about the vandalism done to my t shirt when I went to get dressed. I ventured to the kitchen for some coffee and ran into Cas getting in from a morning run. He blushed when he saw me but otherwise carried on as if the night before _hadn’t_ just blown his friggen mind like it did mine. 

So that’s how it was for a few weeks, insanely awkward and we tried to act like nothing happened. Well, until I saw Cas flirting with some douchebag at the bar. So naturally, me being the cool, calm guy that I am, I slammed my beer on the table so hard it shattered. I know, not my finest moment, but I had shot down everyone that came at me since that night. I only had eyes for Cas, and after having a couple shots and beers in my system did _not_ help when I saw some dude getting cozy with Cas. Charlie yelled at me about my bleeding hand and _that_ caught Cas’ attention. 

I walked to the other end of the bar and grabbed some napkins to slow the blood dripping down my palm when Cas came to check on me. “Here, let me help.”

“I’m good. Don’t you have someone waiting for you?” I pouted. Cas squinted his eyes and tilted his head in confusion. Why does he have to do that when I’m mad at him!? I nodded to the tall guy he was talking with earlier. “Mr. Stick up his ass over there.”

Cas rolled his eyes, clearly exasperated. “I don’t understand you Dean. We’ve been best friends since forever. You never cared who I brought home, much less flirted with. Then you come into my room the other night and we have this _amazing_ night, and the next morning you act as if nothing happened! What do you want Dean!?” 

We didn’t even notice the people starting to stare at this point, my face grew hot and I didn’t even think before I shouted at the top of my lungs, “You Cas! I want you!” Our mirrored expressions must’ve been priceless. Eyes wide as globes, mouths slacked open, unable to speak for what felt like hours. Before I knew it, I started rambling, not giving a damn who heard. “You think I expected this? And _I_ acted like nothing happened!? I was following _your_ lead Cas! You think I just woke up one morning and thought ‘you know what? I’m going to fall in love with my best friend today!’ You think-“ and that was all I could get out before Cas crashed his lips against mine. 

Several people at the bar erupted into applause but it sounded far away like the rest of the world was down a tunnel and only Cas and I were around. When we finally pulled away, breathless he looked at me with those damn ocean blue eyes and smiled. “What took you so long Winchester?”

Look, I don’t even remember how we got home, but once the door swung open, our clothes went flying in all different directions. We made it to my bed and I straddled Cas while I ran my hands through his hair and my teeth raked his bottom lip. I felt his hands explore my entire body and suddenly I realized the elephant in the room. _How are two tops gonna make this work? Shit!_ Cas must’ve sensed exactly what I was thinking because before I could register what was happening, he flipped me onto my back and was now on top of me. 

He leaned down close and gazed into my eyes. “We’ll both try it. But _tonight_ , you’re mine Dean.” A whimper escaped my throat as his heavy, deep voice said my name. I nodded hesitantly and immediately Cas went to work. His mouth assaulted every inch of my body, making me want to beg for sweet relief. Finally he slid my cock down his throat and let his warm saliva drip down to my hole. He slowly worked me open with his fingers while still swirling his tongue around the head of my erection. _Fuck!_ It was so good! 

After the third finger, I was ready to feel him inside me. Now, I wouldn’t bottom for anyone else, but this was Cas and I trusted him with my life _and_ my ass. “Cas, now.” I reached into my nightstand drawer and tossed the bottle of lube I grabbed over to him. He prepped himself and I and slid inside. Not gonna lie, when Cas bottomed out and I was full of _him,_ it felt so good I never wanted it to end. And then he started thrusting. I _really_ didn’t want that to end either. Within minutes I was close to exploding all over the both of us. Cas thrust so hard, my headboard hit the wall and I’m sure it woke up the neighbors. Sorry guys. When he dipped his head so our foreheads touched, he found a new angle. _The_ angle. I couldn’t hold it in any longer, I started moaning, no, screaming my best friend’s name. “Cas! I’m-“

He gripped my shaft and moaned the words I had been waiting to hear. “Come for me baby.” And I did. I came. My vision went black. I heard my voice yell in euphoric bliss, mixed with Cas’ but it didn’t sound like it came from my body. Let me tell you something ladies and gents, bottoming for Cas is _awesome._

We laid there for what felt like hours, gaining our composure. Neither of us could speak. When I finally got my bearings, I lifted myself up and straddled Cas and gave him my best mischievous grin. “Your turn.”

So there ya have it. That’s the story of how my best friend became my boyfriend. And the story of Dean Winchester became a bottom. Until next time folks!


End file.
